2024-03-29T02:25:28Zhttp://digital.csic.es/dspace-oai/requestoai:digital.csic.es:10261/344572022-01-26T08:33:42Zcom_10261_100com_10261_5com_10261_81col_10261_353col_10261_334
One-Pot Synthesis of Polycyclic Nucleosides with Unusual Molecular Skeletons
Bonache, María-Cruz
Cordeiro, Alessandra
Carrero, Paula
Quesada, Ernesto
Camarasa Rius, María José
Jimeno, M. Luisa
San-Félix, Ana
An R hydroxy pyrrolidine tricyclic nucleoside 3 and its spontaneous reaction with acetone is
described. In this transformation highly functionalized polycyclic nucleosides with rather unusual
molecular skeletons are formed in a complete regio-and stereoselective way. The reaction involves
the formation of three new bonds, two of them novel carbon-carbon bonds, in a one-pot way. An
enamine-iminium mechanism with participation of carbinolamine, iminium ion, and enamine
intermediates is proposed as a plausible explanation for this transformation. The scope of the
reaction is briefly studied concluding that the nature of the ketone (R1COR2) is critical for the initial
attack of the NH to the carbonyl group.
2009
artículo
Journal of Organic Chemistry 74 (23) : 9071–9081 (2009)
0022-3263
10261/34457
10.1021/jo9019144
eng
http://dx.doi.org/10.1021/jo9019144
openAccess
American Chemical Society